Microbial models of mammalian metabolism. O-Dealkylation of 10,11-dimethoxyaporphine

Microbial transformations of 10,11-dimethoxyaporphine were studied to determine the potential of microorganisms to produce monomethoxyaporphines. Ten microorganisms were identified as being capable of yielding apocodeine and/or isoapocodeine as the major metabolite in 24 and 20% yield, respectively. Cunninghamella blakesleeana (ATCC 9245) converted 10,11-dimethoxyaporphine quantitatively into isapocodeine. O-Dealkylation of this aporphine system is a facile microbial transformation, and the 10-methoxyl group is more susceptible to metabolic cleavage than the sterically hindered 11-methoxyl group. Selectivity in O-dealkylation may be accomplished with different microorganisms. This is the first report dealing with the microbial transformation of an aporphine system.